Holiday Cookies - Timeline?

I have terribly time management. I am always so afraid of doing things too soon that I end up doing everything too late or not at all.

I have time to make holiday cookies now but have no idea if I can make them now and freeze them, what kind to make, make sugar cookies and decorate and freeze or just freeze then decorate later? Can I make sugar cookies and put chocolate transfers on them and freeze or will the chocolate not be good when it thaws.

I really wish I had someone local who liked to bake and had a good time line on how to do this. *sigh* I need help!

I make my dough, roll into logs and freeze starting in November. Then, when I am ready to bake, it's simply a matter of thawing (or even partially thawing), slicing and baking. You can roll into smaller logs to yield a dozen at a time. Works for me and I do 70 - 80 dozen each Christmas. HTH